JP4463317B2 - 置換イミダゾールおよび殺虫剤としてのその使用 - Google Patents

置換イミダゾールおよび殺虫剤としてのその使用 Download PDF

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Publication number: JP4463317B2
Authority: JP; Japan
Prior art keywords: ethyl; dimethylphenyl; alkylene; imidazole; methyl
Prior art date: 2006-01-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

JP2008550864A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009528979A (ja

Inventor

アンソニーロガンチュブナサン

ロジャーコックスマーク

セバスチャンダウベルグネジェロム

アンドリューエウィンリチャード

ロウレットクリステル

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Ltd Great Britain

Original Assignee

Pfizer Ltd Great Britain

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-01-19

Filing date

2007-01-08

Publication date

2010-05-19

2007-01-08 Application filed by Pfizer Ltd Great Britain filed Critical Pfizer Ltd Great Britain

2009-08-13 Publication of JP2009528979A publication Critical patent/JP2009528979A/ja

2010-05-19 Application granted granted Critical

2010-05-19 Publication of JP4463317B2 publication Critical patent/JP4463317B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-01-08 Anticipated expiration legal-status Critical

Links

239000002917 insecticide Substances 0.000 title description 6
150000002460 imidazoles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 533
-1 R 7 Chemical compound 0.000 claims description 314
125000002947 alkylene group Chemical group 0.000 claims description 152
229910052739 hydrogen Inorganic materials 0.000 claims description 143
239000001257 hydrogen Substances 0.000 claims description 126
125000000217 alkyl group Chemical group 0.000 claims description 124
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 77
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 72
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
150000003839 salts Chemical class 0.000 claims description 55
229910052757 nitrogen Inorganic materials 0.000 claims description 54
229910052799 carbon Inorganic materials 0.000 claims description 53
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 51
125000003545 alkoxy group Chemical group 0.000 claims description 46
125000005843 halogen group Chemical group 0.000 claims description 45
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 37
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
229920006395 saturated elastomer Polymers 0.000 claims description 23
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000004663 dialkyl amino group Chemical group 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
FXJRDUKXWHFPND-NSHDSACASA-N 2-[(1s)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C1([C@@H](C)C=2C(=C(C)C=CC=2)C)=NC=CN1 FXJRDUKXWHFPND-NSHDSACASA-N 0.000 claims description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
FXJRDUKXWHFPND-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1 FXJRDUKXWHFPND-UHFFFAOYSA-N 0.000 claims description 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
235000019260 propionic acid Nutrition 0.000 claims description 5
UXPQTIDCDYNUEW-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-[1-(2,3-dimethylphenyl)ethyl]imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1CC1CC1 UXPQTIDCDYNUEW-UHFFFAOYSA-N 0.000 claims description 4
RYMBPJBTYXXTKV-UHFFFAOYSA-N 1-benzyl-2-[1-(2,3-dimethylphenyl)ethyl]imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1CC1=CC=CC=C1 RYMBPJBTYXXTKV-UHFFFAOYSA-N 0.000 claims description 4
VCQMQYYWJXLGIS-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1-(methoxymethyl)imidazole Chemical compound COCN1C=CN=C1C(C)C1=CC=CC(C)=C1C VCQMQYYWJXLGIS-UHFFFAOYSA-N 0.000 claims description 4
OGBHVDVICPAKRK-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1-[(4-methoxyphenyl)methyl]imidazole Chemical compound C1=CC(OC)=CC=C1CN1C(C(C)C=2C(=C(C)C=CC=2)C)=NC=C1 OGBHVDVICPAKRK-UHFFFAOYSA-N 0.000 claims description 4
JJKXMQNCSXKGST-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1-[[4-(trifluoromethyl)phenyl]methyl]imidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1CC1=CC=C(C(F)(F)F)C=C1 JJKXMQNCSXKGST-UHFFFAOYSA-N 0.000 claims description 4
GICTYBZVKIEHGC-UHFFFAOYSA-N 2-[1-[2-(trifluoromethyl)phenyl]ethyl]-1h-imidazole Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)C1=NC=CN1 GICTYBZVKIEHGC-UHFFFAOYSA-N 0.000 claims description 4
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
LRXDOLSMVZWELC-UHFFFAOYSA-N C(ON1C(=NC=C1)C(C)C1=C(C(=CC=C1)C)C)(OC(C)(C)C)=O Chemical compound C(ON1C(=NC=C1)C(C)C1=C(C(=CC=C1)C)C)(OC(C)(C)C)=O LRXDOLSMVZWELC-UHFFFAOYSA-N 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
FXJRDUKXWHFPND-LLVKDONJSA-N 2-[(1r)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C1([C@H](C)C=2C(=C(C)C=CC=2)C)=NC=CN1 FXJRDUKXWHFPND-LLVKDONJSA-N 0.000 claims description 3
BJONQVBLRBPUNW-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1-ethylimidazole Chemical compound CCN1C=CN=C1C(C)C1=CC=CC(C)=C1C BJONQVBLRBPUNW-UHFFFAOYSA-N 0.000 claims description 3
ZSNGQSFPAPXLRZ-UHFFFAOYSA-N 2-[1-(2,3-dimethylphenyl)ethyl]-1-methylimidazole Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=NC=CN1C ZSNGQSFPAPXLRZ-UHFFFAOYSA-N 0.000 claims description 3
IWOOTJMGZNQLKN-UHFFFAOYSA-N 2-[1-(2,5-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C(C)=CC=C(C)C=1C(C)C1=NC=CN1 IWOOTJMGZNQLKN-UHFFFAOYSA-N 0.000 claims description 3
BFPWWMHMPOMZIB-UHFFFAOYSA-N 2-[1-(3,5-dimethylphenyl)ethyl]-1h-imidazole Chemical compound C=1C(C)=CC(C)=CC=1C(C)C1=NC=CN1 BFPWWMHMPOMZIB-UHFFFAOYSA-N 0.000 claims description 3
DVRSNIFQMIUPPI-UHFFFAOYSA-N 2-[1-(3-methylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=CC(C)=CC=1C(C)C1=NC=CN1 DVRSNIFQMIUPPI-UHFFFAOYSA-N 0.000 claims description 3
PQLXCNZMCQTKHR-UHFFFAOYSA-N 2-[1-(4-chloro-3-methylphenyl)ethyl]-1h-imidazole Chemical compound C=1C=C(Cl)C(C)=CC=1C(C)C1=NC=CN1 PQLXCNZMCQTKHR-UHFFFAOYSA-N 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000004438 haloalkoxy group Chemical group 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 2
125000003566 oxetanyl group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims 1
238000005160 1H NMR spectroscopy Methods 0.000 description 373
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 270
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 228
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 216
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
239000000203 mixture Substances 0.000 description 183
238000002360 preparation method Methods 0.000 description 133
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
239000000243 solution Substances 0.000 description 116
229910001868 water Inorganic materials 0.000 description 108
239000011541 reaction mixture Substances 0.000 description 103
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 93
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
238000002474 experimental method Methods 0.000 description 81
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 64
239000010410 layer Substances 0.000 description 58
238000000034 method Methods 0.000 description 55
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 51
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
125000004435 hydrogen atom Chemical class [H]* 0.000 description 42
238000004262 preparative liquid chromatography Methods 0.000 description 41
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
239000000706 filtrate Substances 0.000 description 38
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
241001465754 Metazoa Species 0.000 description 31
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 29
238000009472 formulation Methods 0.000 description 29
239000012074 organic phase Substances 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
239000000651 prodrug Substances 0.000 description 28
229940002612 prodrug Drugs 0.000 description 28
125000006239 protecting group Chemical group 0.000 description 27
238000011282 treatment Methods 0.000 description 25
238000006243 chemical reaction Methods 0.000 description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 24
239000000377 silicon dioxide Substances 0.000 description 24
239000000284 extract Substances 0.000 description 23
235000017557 sodium bicarbonate Nutrition 0.000 description 23
229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
239000000010 aprotic solvent Substances 0.000 description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
229910052763 palladium Inorganic materials 0.000 description 20
239000002585 base Substances 0.000 description 19
230000015572 biosynthetic process Effects 0.000 description 19
241000238876 Acari Species 0.000 description 18
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 18
241000607479 Yersinia pestis Species 0.000 description 17
239000002253 acid Substances 0.000 description 17
125000001309 chloro group Chemical group Cl* 0.000 description 17
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 16
229910000024 caesium carbonate Inorganic materials 0.000 description 16
125000004356 hydroxy functional group Chemical group O* 0.000 description 16
239000004480 active ingredient Substances 0.000 description 15
239000012298 atmosphere Substances 0.000 description 15
239000003814 drug Substances 0.000 description 15
125000001153 fluoro group Chemical group F* 0.000 description 15
239000000047 product Substances 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000000126 substance Substances 0.000 description 15
241000238421 Arthropoda Species 0.000 description 14
239000003153 chemical reaction reagent Substances 0.000 description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 14
239000012267 brine Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 13
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
241000196324 Embryophyta Species 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
244000045947 parasite Species 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000012453 solvate Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
230000008569 process Effects 0.000 description 11
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 10
239000008346 aqueous phase Substances 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
125000000524 functional group Chemical group 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
238000005984 hydrogenation reaction Methods 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
239000002243 precursor Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
230000014759 maintenance of location Effects 0.000 description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
239000008194 pharmaceutical composition Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
241000238631 Hexapoda Species 0.000 description 8
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239000006188 syrup Substances 0.000 description 1
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239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
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238000010998 test method Methods 0.000 description 1
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208000016523 tick-borne infectious disease Diseases 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000011426 transformation method Methods 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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238000005292 vacuum distillation Methods 0.000 description 1
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239000000811 xylitol Substances 0.000 description 1
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235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP2008550864A 2006-01-19 2007-01-08 置換イミダゾールおよび殺虫剤としてのその使用 Expired - Fee Related JP4463317B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76076506P	2006-01-19	2006-01-19
PCT/IB2007/000071 WO2007083207A1 (en)	2006-01-19	2007-01-08	Substituted imidazoles and their use as pesticides

Publications (2)

Publication Number	Publication Date
JP2009528979A JP2009528979A (ja)	2009-08-13
JP4463317B2 true JP4463317B2 (ja)	2010-05-19

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Country Status (31)

Country	Link
US (4)	US7592362B2 (de)
EP (2)	EP1981853B1 (de)
JP (1)	JP4463317B2 (de)
KR (1)	KR101044494B1 (de)
CN (1)	CN101370786B (de)
AR (1)	AR059055A1 (de)
AT (1)	ATE505461T1 (de)
AU (1)	AU2007206698B2 (de)
BR (1)	BRPI0707185B8 (de)
CA (1)	CA2632771C (de)
CY (1)	CY1111473T1 (de)
DE (1)	DE602007013869D1 (de)
DK (1)	DK1981853T3 (de)
EA (1)	EA015738B1 (de)
ES (1)	ES2362935T3 (de)
IL (1)	IL192063A0 (de)
MA (1)	MA30166B1 (de)
ME (2)	MEP4208A (de)
MY (1)	MY145812A (de)
NO (1)	NO341141B1 (de)
NZ (1)	NZ569209A (de)
PL (1)	PL1981853T3 (de)
PT (1)	PT1981853E (de)
RS (1)	RS53512B1 (de)
SI (1)	SI1981853T1 (de)
TN (1)	TNSN08306A1 (de)
TW (1)	TWI337998B (de)
UA (1)	UA93696C2 (de)
UY (1)	UY30096A1 (de)
WO (1)	WO2007083207A1 (de)
ZA (1)	ZA200805565B (de)

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2007
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Also Published As

Publication number	Publication date
MEP4208A (en)	2010-06-10
SI1981853T1 (sl)	2011-08-31
AU2007206698B2 (en)	2011-11-03
KR20080085046A (ko)	2008-09-22
CA2632771C (en)	2011-03-22
US20080119536A1 (en)	2008-05-22
NO20083404L (no)	2008-08-04
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